O-Phenylenediamine → HCID 44623633, compound

HRID 415947Notes

Reaction equation

HRID 415947 reaction equation
[CH:1]1([N:4]2[CH2:9][CH2:8][N:7]([C:10]3[N:15]=[CH:14][C:13]([C:16]4[N:17]=[C:18]([C:21]5([C:27]6[CH:35]=[CH:34][C:30]([C:31]([OH:33])=O)=[CH:29][CH:28]=6)[CH2:26][CH2:25][O:24][CH2:23][CH2:22]5)[S:19][CH:20]=4)=[CH:12][CH:11]=3)[CH2:6][CH2:5]2)[CH2:3][CH2:2]1.[C:36]1([NH2:43])[C:37]([NH2:42])=[CH:38][CH:39]=[CH:40][CH:41]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[NH2:42][C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][C:36]=1[NH:43][C:31](=[O:33])[C:30]1[CH:29]=[CH:28][C:27]([C:21]2([C:18]3[S:19][CH:20]=[C:16]([C:13]4[CH:14]=[N:15][C:10]([N:7]5[CH2:8][CH2:9][N:4]([CH:1]6[CH2:2][CH2:3]6)[CH2:5][CH2:6]5)=[CH:11][CH:12]=4)[N:17]=3)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]2)=[CH:35][CH:34]=1

Participants

6

Reactant 4

HCID 7243O-PhenylenediamineHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66619342HCID 66619342, compound

Product 1

HCID 44623633HCID 44623633, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(4-{4-[6-(4-cyclopropyl-piperazin-1-yl)-pyridin-3-yl]-thiazol-2-yl}-tetrahydro-pyran-4-yl)-benzoic acid (60 mg, 0.122 mmol), benzene-1,2-diamine (26 mg, 2.0 eq), HATU (56 mg, 1.2 eq), and DIPEA (0.042 mL, 2.1 eq) were dissolved in DMF and stirred at room temperature for 2 hours. After the reaction was complete, the reaction mixture was extracted with EtOAc and water. The organic phase was dried with MgSO4 and evaporated. The solid was purified by reverse phase chromatography to afford title compound. MS found for C33H36N6O2S as (M+H)+ 581.56. 1H NMR (400 MHz, dmso-d6): δ: 9.24 (s, 1H), 8.35 (s, 1H), 7.68 (d, J=6.2 Hz, 1H), 7.60 (d, J=8.2 Hz, 2H), 7.51 (s, 1H), 7.23 (d, J=8.4 Hz, 2H), 6.79 (d, J=7.2 Hz, 1H), 6.62-6.51 (m, 2H), 6.41 (d, J=7.4 Hz, 1H), 6.22 (t, J=5.2 Hz, 1H), 4.51 (s, 2H), 3.45-3.38 (m, 2H), 3.32-3.25 (m, 2H), 3.18-3.11 (m, 4H), 2.38-2.22 (m, 6H), 2.15-2.05 (m, 2H), 1.31-1.23 (m, 1H), 0.12-0.1 (m, 4H).

Workup

  1. extractionthe reaction mixture was extracted with EtOAc and water
  2. dry with materialThe organic phase was dried with MgSO4
  3. customevaporated
  4. customThe solid was purified by reverse phase chromatography

Sources & evidence

ORD record
ord-12e491a60cc34d5db983a5ca1cfb473a
Source dataset
uspto-grants-2012_01
Patent number
US08088771B2

Reaction notes

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